Tool boxes you want something decent.
The ONLY cheap brand that I would buy is Harbor Freight US General (the red box), everything else isn't worth it including Craftsman, Lowes, Home Depot, Kragen, etc...
Tools you have to evaluate the tool to determine the brand, each company has their specialty. I wouldn't shy away from Craftsman wrenches and getting them replaced is much easier then Snap On or Matco. If you have Matco tools and something breaks, it's harder to get it swapped out if you don't work in a shop. The shop guys see their Matco guys and unless you have a friend you won't.
Craftsman screw drivers, wrenches, ratcheting wrenches, etc... are good.
Craftsman makes a quality ratchet and cheap ratchet, their 180 tooth ratchet is nice and worth the money IMO.
It sounds like you have a basic socket set and there is no reason not to stick with Craftsman, if you break a socket run down to Sears and get it swapped out.
Impact sockets are another story, DO NOT buy cheap. One of those comes apart in your hand and you might lose your hand. It's not safe and you should buy quality impact sockets. Also never put a standard socket on an impact.
Air Compressors, you need to do your research. I've had fairly good luck using a Craftsman, but you need to really evaluate what you are using it for. Duty cycle is important, if you are painting a Craftsman won't keep up. Also oil free vs oil air compressors come into play depending on what you are using it for.
Impacts... I'm a fan of IR, they are a good quality impact. You can buy an IR impact at your local Sears. If you get a cheap impact or air tool it won't hold up or do half the work you need it to. I've seen brand new impacts unable to pull off a lug nut.
Kobalt tools from Lowes used to be made by Snap On, but are now cheap chinese tools. One of the few tools I would buy from them is their set of small needle nose pliers, dikes, etc... I bought a set for a project my girl was working on and was so impressed I bought a set for myself. I honestly like them better then my Matco and Craftsman.
I have MOSTLY Matco tools, followed by Craftsman, and a few other tools from other various places like Snap On, Lowes, etc...
As far as an OBD2 scanner, this gets real complicated, but they make some nice computer interface scanners that let you data log and check any OBD2 system via your computer. If you want to get crazy, I'm pretty happy with my Snap On Solus Pro, but it's expensive to keep up to date.
Cordless Re-Chargeable Impacts - I don't have a lot of experience here, but I was told that the ones from Lowes are great and hold up pretty good. I have a Matco 1/2" impact and it's great, but pricey. If you use these a lot you plan on them to wear out.
Wobbly Sockets, I suggest buying Impact wobbly sockets, because you can use them with or without an impact. Again, this is something that should come from Matco or Snap On. I personally have Matco. Also you can get wobbly extensions that work in a lot of situations with standard sockets / impact sockets.
Torque Wrench - I would spend some $$ here or get something quality. There is a vendor on Duramax Diesels that sells Torque Wrenches out a discount to Duramax enthusiasts. I don't know anybody who has bought them, but they are fairly cheap and claim to be great quality.
Floor Jack, Trans Jack, etc... - I always buy these at Harbor Freight and have never had an issue. You can get some nice ones capable of lifting our trucks for a reasonable price. Always remember to use jack stands on a level surface though. Also be aware what you are doing, especially if you are using a cheater/breaker bar.
A friend of mine was under his Impala working and when he puled down on his breaker bar it had enough force to unbalance the car where it fell off the jackstands on top of him. He was pinned under it until a neighbor boy helped get him out from under it. He permanently lost the ability to feel anything in one arm and was lucky to come out alive. A good idea is to place your tires/rims under the frame when you have the car / truck up too... That is just a secondary safety measure to give you as much space if it did fall so it didn't go "splat".